Risky Business: Taking Big Risks in Your Writing Career—and How They Can Pay Off

In the “Risky Business” feature in our September issue, we talked with other writers who had taken big risks in their writing careers and how it had paid off—along with what they learned along the way. We didn’t have room to share all their insights in print, but we’ve included them here.

Truth: These bold strategies will help push you forward at any stage of the writing career. So give them a try—we dare you.

How did you know that it was time to pursue freelance full time?

“I set a very firm boundary of ‘If I don’t make X amount by Y date, I’m going back to law.’ This gave me a set deadline for experimentation, encouraged more ambitious projects and overall kept me focused on what I was doing and why.”

“Consider the alternative: You could choose not to write. You could push these desires to the side and continue doing what you’re doing. The writers who really feel called to write will realize that the alternative just isn’t an option.”

What was the first step you took in preparing to support yourself?

“There wasn’t much preparation before diving headfirst into freelancing. No savings built up. No pre-launch marketing. I had a solid foundation in business, marketing and PR from my education and past employment. That’s what kept my head above water.”

“It’s very important to have a plan B. When I quit my job as a lawyer, I still had my bar admission and a law degree. Make a list of all the skills you’re good at and see where you can eke out a different trajectory if this won’t work. Or better still, to try them both—skills for something new, writing on the side. You never know where it will lead you.”

What gave you the courage to make the leap?

“I knew something had to change when I was having trouble sleeping. When I was tossing and turning, I knew, deep down, that I wasn’t living the life I was supposed to be living—and that broke my heart. I just couldn’t do it anymore. As soon as I went all in and committed to pursuing my writing, I felt a huge weight being lifted off my shoulders.”

—Rigby

…

“The scariest part of taking a chance was not knowing that it would work, how it would work, or how quickly it would work. I didn’t want to just quit cold turkey and spend the next few months scrambling for clients and not knowing when I’d be stable. So I made myself a deal: I would quit my ad agency job, but I would also get a new job temporarily while I started the business.

Over about six months, while working that new job, I took a business-writing course at the local chamber of commerce. I attended networking events. I put up a website. And I started telling every person I knew that I was looking for freelance copywriting work.

I made myself a promise. I could quit the new job when either, A) I had enough clients that I literally could not take on more work without quitting, or B) I had enough money in the bank to cover expenses for a year with no income.

About six months into the corporate job, I achieved A.

I’m pretty risk-averse, so this slow move into freelancing was definitely the best choice for me. It helped me mitigate my stress and set up a foundation for the business before leaving a more steady income source.”

What aspects of being a full-time writer surprised you the most?

“What’s surprised me is the sheer amount of pitching you have to do! It’s seriously time-consuming work.”

—Rigby

What advice would you offer writers considering a fresh start?

“See what’s missing in the marketplace, whether that’s your voice that differs from someone else’s, a product you feel can fix a ‘pain point,’ a unique something that speaks to your work. In my case, my site brought in readers, but I did not take sponsored posts or press trips as a business model. Instead, I developed products I hoped would be useful to my community. The first was my book, The Food Traveler’s Handbook, the second was food walks (where I took readers around Saigon and Oaxaca on street-food crawls), and then came celiac translation cards and my hand-drawn maps of food. Each of these is appealing to a different demographic of my readers, but they all fall in line with who I am as a writer, and as a person.”

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